Stereoselective approaches to (E,E,E) and (Z,E,E)-α-chloro-ω-substituted hexatrienes:: Synthesis of all E polyenes

被引：35
作者：
Crousse, B
Mladenova, M
Ducept, P
Alami, M
Linstrumelle, G
机构：
[1] Ecole Normale Super, CNRS, Dept Chim, F-75231 Paris 05, France
[2] Bulgarian Acad Sci, Inst Organ Chem, BG-1113 Sofia, Bulgaria
来源：
TETRAHEDRON | 1999年 / 55卷 / 14期
关键词：
D O I：
10.1016/S0040-4020(99)00123-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two stereocontrolled synthetic approaches to (E,E,E) and (Z,E,E)-alpha-chloro-omega-substituted hexatrienes 1-3 are described starting from unsaturated compounds 4-6. The key step of the first approach is based on the palladium-catalyzed rearrangement of bis-allylic acetates 4 and 5 and the second one is based on the stereoselective reduction of homopropargylic alcohols 6 followed by an elimination reaction. These stable chlorotrienes 1-3 are suitable synthetic intermediates for the construction of navenone B and all E polyenes (trienes, tetraenes, hexaenes and heptaenes). (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码：4353 / 4368
页数：16
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